- A chemoselective approach to functionalize the C-10 position of 10- deacetylbaccatin III. Synthesis and biological properties of novel C-10 Taxol analogues
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A chemoselective approach to functionalize the C-10 position of 10- deacetyl baccatin III, a key intermediate for the semi-synthesis of paclitaxel, is described. The chemistry provides an easy access to a variety of C-10 hydroxyl derivatives, such as, eth
- Kant,O'Keeffe,Chen,Farina,Fairchild,Johnston,Kadow,Long,Vyas
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Read Online
- Total Synthesis of Paclitaxel
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The total synthesis of paclitaxel (Taxol) is described. Double Rubottom oxidation of the bis(silyl enol ether) derived from a tricarbocyclic diketone effectively installed a bridgehead olefin and C-5/C-13 hydroxy groups in a one-step operation. The novel Ag-promoted oxetane formation smoothly constructed the tetracyclic framework of paclitaxel.
- Iiyama, Shota,Fukaya, Keisuke,Yamaguchi, Yu,Watanabe, Ami,Yamamoto, Hiroaki,Mochizuki, Shota,Saio, Ryosuke,Noguchi, Takashi,Oishi, Takeshi,Sato, Takaaki,Chida, Noritaka
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p. 202 - 206
(2021/12/27)
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- Fluorinated taxane compound, preparation method therefor and application of fluorinated taxane compound
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The invention discloses a fluorinated taxane compound, a preparation method therefor and an application of the fluorinated taxane compound. The compound has a structural general formula represented bya formula I. Proven by pharmacological experiments, compared with paclitaxel, a series of fluorinated taxane derivatives synthesized by the method have cytotoxicity superior to that of the paclitaxelto a multidrug-resistant human mammary cancer cell line MCF-7/Adr and an ovarian cancer cell line NCI/Adr and represent cytotoxicity superior to that of the paclitaxel to a colon cancer cell line HCT-116 with overexpressed neoplasm stem cells.
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- Novel crystalline forms of anticancer compound CX1409 and preparation method and application of novel crystalline forms of anticancer compound CX1409
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The invention relates to the field of compounds, in particular to two novel crystalline forms of an anticancer compound CX1409. A crystalline form A of the anticancer compound CX1409 is determined byusing a powder X-ray diffraction method, wherein characteristic diffraction peaks are shown at 4.3 degree, 8.7 degree, 11.0 degree, 12.5 degree, 13.0 degree, 14.1 degree, 15.4 degree, 17.4 degree, 18.4 degree, 19.6 degree, 20.1 degree, 20.8 degree, 21.7 degree, 27.0 degree, 29.0 degree, 30.6 degree and 31.4 degree in an X-ray powder diffraction spectrum expressed by a diffraction angle of 2 theta+/-0.3 degree; a crystalline form B of the anticancer compound CX1409 is determined by using the powder X-ray diffraction method, wherein characteristic diffraction peaks are shown at 4.9 degree, 5.4degree, 5.8 degree, 6.4 degree, 8.0 degree, 9.4 degree and 12.9 degree in an X-ray powder diffraction spectrum expressed by a diffraction angle of 2 theta +/-0.3 degree. The above two crystalline forms are not reported, outlines of the two crystalline forms are clear, and the two crystalline forms can be perfectly reproduced; besides, the two crystalline forms have the advantages of being good instability of preparation and high in yield and purity, can be applied to anti-tumor drugs, and have wide application prospects.
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Paragraph 0056
(2018/04/01)
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- Anticancer compound CX1409 dihydrate and DMSO solvate of the new crystal and its preparation method and application (by machine translation)
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The invention relates to the field of compound, in particular to anti-cancer compounds CX1409 of the dihydrate and DMSO solvate of the two new crystalline form, wherein the anticancer compound CX1409 dihydrate crystalline forms of powder X-ray diffraction for C assay measuring, in order to 2 θ ± 0.3 ° diffraction of said X-ray powder diffraction spectrum in the 5.0 °, 5 . 8°, 10 . 4°, 12 . 8°, 13 . 6°, 15 . 2°, 18 . 6°, 20 . 0°, 20 . 7°, 21 . 6°, 22 . 1° and 22.8 ° for display at the feature diffraction peak. Anticancer compound CX1409 of DMSO solvate crystalline forms of powder X-ray diffraction for D assay measuring, in order to 2 θ ± 0.3 ° diffraction of said X-ray powder diffraction spectrum in the 8.1 °, 8 . 6°, 11 . 1°, 11 . 4°, 12 . 4°, 13 . 0°, 13 . 8°, 14 . 2°, 14 . 8°, 15 . 3°, 15 . 8°, 17 . 2°, 18 . 0°, 18 . 2°, 19 . 7°, 20 . 0° and 22.3 ° for display at the feature diffraction peak. The above two kinds of crystalline form has not been reported, the contours thereof are clear, and can be perfectly reproducing, and has good stability, high yield, purity is high, can be used as the use of the antineoplastic, it has broad application prospects. (by machine translation)
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Paragraph 0075; 0076; 0077
(2018/03/25)
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- Antagonizing NOD2 Signaling with Conjugates of Paclitaxel and Muramyl Dipeptide Derivatives Sensitizes Paclitaxel Therapy and Significantly Prevents Tumor Metastasis
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A noncleavable paclitaxel (PTX) and N-acetylmuramyl-l-alanyl-d-isoglutamine (MDP) derivative conjugate, 22 (DY-16-43), and its analogues were prepared and characterized as antagonists of NOD2 signaling. This conjugate enhanced the antitumor and antimetastatic efficacy of PTX in Lewis lung carcinoma (LLC) tumor-bearing mice. This work first describes a molecular strategy that enables the sensitization of a chemotherapeutic response via antagonizing NOD2 inflammatory signaling and suggests NOD2 antagonist as potential adjunct in treating non-small-cell lung cancer (NSCLC).
- Dong, Yi,Wang, Suhua,Wang, Chunting,Li, Zihua,Ma, Yao,Liu, Gang
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p. 1219 - 1224
(2017/02/19)
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- Methods for preparing semi-synthetic paclitaxel and intermediate thereof
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The invention relates to methods for preparing semi-synthetic paclitaxel and an intermediate thereof. The method for preparing the semi-synthetic paclitaxel comprises the following steps: dissolving 10-DABIII (10-deacetylbaccatinIII) into pyridine, protecting hydroxyl on position-7 carbon on the 10-DABIII with triethyl silicyl to obtain an intermediate I, acetylating hydroxyl on position-10 carbon of the intermediate I to obtain an intermediate II, reacting the intermediate II, a side-chain radical compound and 4-dimethylaminopyridine in an organic solvent to prepare an intermediate III, and reacting the intermediate III with trifluoroacetic acid under an acidic condition to obtain a crude paclitaxel product. The preparation methods are simple and easy for industrialization; the active hydroxyl of the raw material 10-DABIII is effectively protected, so that fewer byproducts are finally generated, and a prepared paclitaxel product has high molar yield of 70 to 81 percent and high paclitaxel purity of 99.5 to 99.9 percent; the residual rate of the raw material in the steps of synthesizing the intermediate II and synthesizing the paclitaxel is low, side reactions are reduced, and the raw material is high in reaction selectivity and utilization rate; the product can be directly used as a raw material for the medical field of treatment of ovarian cancer, breast cancer and the like.
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- A process for the preparation of paclitaxel
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The invention discloses a preparation method of paclitaxel. A side chain which performs condensation reaction on 13-hydroxyl of 7-TES-barca III is di(3R, 4S)-1-benzoyl-3-hydroxyl-4-phenylazepane-2-butanone. According to the preparation method, a new side chain is used for performing condensation reaction; a new preparation method is expanded, the quantity of reaction byproducts is small, and the yield is high.
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Paragraph 0074-0075
(2018/02/04)
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- Ferrocenyl Paclitaxel and Docetaxel Derivatives: Impact of an Organometallic Moiety on the Mode of Action of Taxanes
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A series of ferrocenyl analogues and derivatives of paclitaxel and docetaxel were synthesised and assayed for their antiproliferative/cytotoxic effects, impact on the cell cycle distribution and ability to induce tubulin polymerisation. The replacement of the 3′-N-benzoyl group of paclitaxel with a ferrocenoyl moiety, in particular, led to formation of an analogue that was at least one order of magnitude more potent in terms of antiproliferative activity than the parent compound (IC50values of 0.11 versus 1.11 μm, respectively), but still preserved the classical taxane mode of action, that is, microtubule stabilisation leading to mitotic arrest. Molecular docking studies revealed an unexpected binding pocket in the tubulin structure for the ferrocenoyl group introduced in the paclitaxel backbone.
- Wieczorek, Anna,B?au?, Andrzej,?al, Aleksandra,Arabshahi, Homayon John,Reynisson, Jóhannes,Hartinger, Christian G.,Rychlik, B?a?ej,Pla?uk, Damian
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supporting information
p. 11413 - 11421
(2016/08/03)
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- A structure-based design of new C2- and C13-substituted taxanes: Tubulin binding affinities and extended quantitative structure-activity relationships using comparative binding energy (COMBINE) analysis
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Ten novel taxanes bearing modifications at the C2 and C13 positions of the baccatin core have been synthesized and their binding affinities for mammalian tubulin have been experimentally measured. The design strategy was guided by (i) calculation of interaction energy maps with carbon, nitrogen and oxygen probes within the taxane-binding site of β-tubulin, and (ii) the prospective use of a structure-based QSAR (COMBINE) model derived from an earlier series comprising 47 congeneric taxanes. The tubulin-binding affinity displayed by one of the new compounds (CTX63) proved to be higher than that of docetaxel, and an updated COMBINE model provided a good correlation between the experimental binding free energies and a set of weighted residue-based ligand-receptor interaction energies for 54 out of the 57 compounds studied. The remaining three outliers from the original training series have in common a large unfavourable entropic contribution to the binding free energy that we attribute to taxane preorganization in aqueous solution in a conformation different from that compatible with tubulin binding. Support for this proposal was obtained from solution NMR experiments and molecular dynamics simulations in explicit water. Our results shed additional light on the determinants of tubulin-binding affinity for this important class of antitumour agents and pave the way for further rational structural modifications. The Royal Society of Chemistry 2013.
- Coderch, Claire,Tang, Yong,Klett, Javier,Zhang, Shu-En,Ma, Yun-Tao,Shaorong, Wang,Matesanz, Ruth,Pera, Benet,Canales, Angeles,Jimenez-Barbero, Jesus,Morreale, Antonio,Diaz, J. Fernando,Fang, Wei-Shuo,Gago, Federico
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p. 3046 - 3056
(2013/07/26)
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- PROCESS FOR PREPARING TAXOIDS FROM BACCATIN DERIVATIVES USING LEWIS ACID CATALYST
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The present invention relates to a process of preparing a taxoid (X) by reacting a protected baccatin derivative (B) with a β-lactam (C) in the presence of one or more Lewis acids and a base agent. The present invention also relates to a process of preparing the protected baccatin derivative (B) from a baccatin derivative (A) comprising a protection reaction catalyzed by one or more Lewis acids with an optional base agent.
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- Synthesis of deuterium-labelled paclitaxel and its hydroxyl metabolite
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This paper describes the synthesis of deuterium-labelled paclitaxel and its hydroxyl metabolite. Paclitaxel labelled with 2H was obtained in four steps using the commercially available [2H5]benzoic chloride as the stable l
- Tian, Lei,Wu, Keying,Tao, Jie,Chen, Liqin
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experimental part
p. 318 - 323
(2012/02/03)
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- Synthesis of 4-deacetyl-1-dimethylsilyl-7-triethylsilylbaccatin III
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A one-pot trisilylation step to protect three hydroxyl groups of baccatin III (1), followed by hydride ester cleavage and base hydrolysis of a triethylsilyl ether at C13, provides efficient access to a key intermediate 9 (top path). This route removes two
- Ondari, Mark E.,Walker, Kevin D.
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scheme or table
p. 2186 - 2188
(2009/08/07)
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- Design, synthesis, and biological evaluation of new-generation taxoids
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Novel second-generation taxoids with systematic modifications at the C2, C10, and C3′N positions were synthesized and their structure-activity relationships studied. A number of these taxoids exhibited exceptionally high potency against multidrug-resistan
- Ojima, Iwao,Chen, Jin,Sun, Liang,Borella, Christopher P.,Wang, Tao,Miller, Michael L.,Lin, Songnian,Geng, Xudong,Kuznetsova, Larisa,Qu, Chuanxing,Gallager, David,Zhao, Xianrui,Zanardi, Ilaria,Xia, Shujun,Horwitz, Susan B.,Mallen-St. Clair, Jon,Guerriero, Jennifer L.,Bar-Sagi, Dafna,Veith, Jean M.,Pera, Paula,Bernacki, Ralph J.
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scheme or table
p. 3203 - 3221
(2009/05/11)
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- Method for Preparing Paclitaxel
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The invention concerns a method for preparing paclitaxel characterized in that it consists in starting with 10-deacety)-baccatine in accordance with a “one-pot” reaction including the following three steps: a) protecting the hydroxy radical in position 7 of 10-deacetylbaccatine with a silylated radical, then b) acetylating the hydroxy radical in position 10, c) optionally crystallizing the resulting baccatine III derivative, followed by condensation of (4S,5R)-3-N-benzoyl-2RS-methoxy-4-phenyl-1,3-oxazolidine-5-carboxylic acid, by esterifying in position 13 the acetylated 10-baccatine III derivative previously obtained, then opening the oxazolidine of the cyclic side chain and simultaneously releasing the hydroxy radical in position 7.
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Page/Page column 2
(2008/12/08)
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- A facile one-pot synthesis of 7-triethylsilylbaccatin III
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A one-pot synthesis of 7-triethylsilylbaccatin III has been delineated. The reaction can easily be extended for the preparation of analogs of baccatin III.
- Baloglu, Erkan,Miller, Michael L.,Cavanagh, Emily E.,Marien, Tracy P.,Roller, Elizabeth E.,Chari, Ravi V. J.
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p. 817 - 818
(2007/10/03)
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- Facile method for synthesizing baccatin III compounds
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A process for synthesizing a C-7 protected baccatin III compound represented by formula (A), which comprises reacting a 10-deacetylbaccatin III compound represented by formula (B) with a protecting agent and an acylating agent in the presence of a secondary amine and a nitrogen-containing compound. Also, a process for synthesizing a C-7 protected 10-deacetylbaccatin III compound represented by formula (C), which comprises reacting a 10-deacetylbaccatin III compound represented by formula (B) with a protecting agent in the presence of a secondary amine and a nitrogen-containing compound. In both processes the nitrogen-containing compound is selected from a nitrogen-containing heterocycle or a trialkylamine. When the nitrogen-containing heterocycle is selected, it may be an unsubstituted or a substituted pyridine or an unsubstituted or a substituted pyrazine. When a trialkylamine is selected, it may be, for example, triethylamine or diisopropylethylamine. wherein PG1 represents the organic residue of the protecting agent, PG2 represents the organic residue of the acylating agent, and R represents a simple or substituted aryl group or a heterocyclic group.
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Page/Page column 9
(2010/02/14)
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- Structure-activity relationship study of taxoids for their ability to activate murine macrophages as well as inhibit the growth of macrophage-like cells
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A series of new taxoids modified at the C-3′, C-3′N, C-10, C-2 and C-7 positions has been designed, synthesized and evaluated for their potency to induce NO and TNF production by peritoneal murine macrophages (Mφ) from LPS-responsive C3H/HeN and LPS-hyporesponsive C3H/HeJ strains and human blood cells, and for their ability to inhibit the growth of Mφ-like cell lines J774.1 and J7.DEF3. The SAR-study has shown that the nature of the substituents at these positions have critical effect on the induction of TNF and NO production by Mφ. Positions C-3′ and C-10 are the most flexible and an intriguing effect of the length of the substituents at the C-10 position is observed for taxoids bearing a straight chain alkanoyl moiety. An aromatic group at the C-3′N and C-2 positions is required for the activity, while only hydroxyl or acetyl substituents seem to be tolerated at the C-7 position. The natural stereochemistry in the C-13 isoserine side chain of the taxoids is an absolute requirement for macrophage activation. It has also been clearly shown that there is no correlation between the ability of the taxoids to induce TNF/NO production in C3H/HeN Mφ and the cytotoxicity against Mφ-like cells.
- Ojima, Iwao,Fumero-Oderda, Cecilia L.,Kuduk, Scott D.,Ma, Zhuping,Kirikae, Fumiko,Kirikae, Teruo
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p. 2867 - 2888
(2007/10/03)
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- Taxanes having an alkyl substituted side-chain and pharmaceutical compositions containing them
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Taxane derivatives having an alkyl substituted C13 side chain.
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Page column 8
(2010/01/30)
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- Beta-Lactams useful for preparation of substituted isoserine esters using metal alkoxides
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β-lactams are disclosed which are useful for preparing N-acyl, N-sulfonyl and N-phosphoryl substituted esters by reaction with a metal alkoxide.
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- A facile N-debenzoylation of paclitaxel: Conversion of paclitaxel to docetaxel
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An efficient and regioselective method for the N-debenzoylation of paclitaxel has been developed, and has been applied to the conversion of paclitaxel to 10-acetyldocetaxel and to docetaxel.
- Jagtap,Kingston
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p. 189 - 192
(2007/10/03)
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- New photoaffinity analogs of paclitaxel
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Two new photoreactive paclitaxel analogs bearing [3H2]-3-(4- benzoyl)phenylpropanoyl group as the photophore as well as radiolabeling unit at the 7 and 10 positions, respectively, are developed. These new photoreactive analogs showed
- Ojima, Iwao,Bounaud, Pierre-Yves,Ahern, David G.
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p. 1189 - 1194
(2007/10/03)
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- Asymmetric total synthesis of Taxol
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The asymmetric total synthesis of Taxol was achieved by way of B to BC to ABC to ABCD ring construction. Optically active 8-membered ring enones 1 and 2 corresponding to the B ring of Taxol have been synthesized in high yields from the linear precursors 28 and 32, respectively, by intramolecular aldol cyclization using SmI2. The optically active linear polyoxy compounds 28 and 32 were obtained by way of diastereoselective aldol reaction between aldehyde 4 and ketene silyl acetal 8 catalyzed by MgBr2 · OEt2. The chiral pentanal 4 was synthesized either by asymmetric aldol reaction of achiral aldehyde 7 and ketene silyl acetal 8 by means of a chiral Lewis acid or by diastereoselective aldol reaction between the chiral aldehyde 16, derived from L-serine, and the lithium enolate derived from methyl isobutyrate. Optically active bicyclo[6.4.0]dodecanone 38β, corresponding to the BC ring system of Taxol, was prepared from 8-membered ring enone 2 in high yield by stereoselective Michael addition and successive intramolecular aldol cyclization. Furthermore, baccatin III, the ABCD ring system of Taxol, was efficiently synthesized from the BC ring system 38β by successive construction of the A and D rings by intramolecular pinacol coupling cyclization, introduction of the C-13 hydroxyl group and an oxetane-forming reaction. Finally, the total synthesis of Taxol was accomplished by dehydration condensation between a protected N-benzoylphenylisoserine 70 or 75 and 7-TES baccatin III, prepared from baccatin III. Taxol side chains 70, 73, 75, and 77, optically active protected N-benzoylphenylisoserines, were synthesized by enantioselective aldol reaction from two achiral starting materials, benzaldehyde and an enol silyl ether 65 derived from S-ethyl benzyloxyethanethioate.
- Mukaiyama, Teruaki,Shiina, Isamu,Iwadare, Hayato,Saitoh, Masahiro,Nishimura, Toshihiro,Ohkawa, Naoto,Sakoh, Hiroki,Nishimura, Koji,Tani, Yu-Ichirou,Hasegawa, Masatoshi,Yamada, Koji,Saitoh, Katsuyuki
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p. 121 - 161
(2007/10/03)
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- New taxanes as highly efficient reversal agents for multidrug resistance in cancer cells
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New non-cytotoxic taxanes synthesized from 10-deacetylbaccatin III and special hydrophobic acylating agents show remarkable MDR reversal activity (≤99.8%) against drug-resistant human breast cancer cells when co-administered with paclitaxel or doxorubicin. This activity is ascribed to the highly efficient blocking of P-glycoprotein efflux by these new taxanes.
- Ojima, Iwao,Bounaud, Pierre-Yves,Takeuchi, Craig,Pera, Paula,Bernacki, Ralph J.
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p. 189 - 194
(2007/10/03)
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- Total asymmetric synthesis of taxol by dehydration condensation between 7-TES baccatin III and protected N-benzoylphenylisoserines prepared by enantioselective aldol reaction
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Total asymmetric synthesis of Taxol was completed by dehydration condensation between a protected N-benzoylphenylisoserine 4 or 9 and 7-TES baccatin in which was prepared from 8-membered ring enone. Taxol side chains 4, 7, 9 and 11, optically active protected N-benzoylphenylisoserines, were successfully synthesized by enantioselective aldol reaction from two achiral starting materials, benzaldehyde and an enol silyl ether derived from S-ethyl benzyloxyethanethioate.
- Shiina, Isamu,Saitoh, Katsuyuki,Frechard-Ortuno, Isabelle,Mukaiyama, Teruaki
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- New and effective synthesis of 7-triethylsilylbaccatin III from 7β,13α-bistriethylsiloxy-1β,2α,10β-trihydroxy-9-oxo- 4(20),11-taxadiene
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7β,13α-Bistriethylsiloxy-1β,2α,10β-trihydroxy -9- oxo-4(20), 11-taxadiene (2), derived from 10-deacetylbaccatin III via degradation of oxetane ring, was conveniently converted into 7-triethylsilylbaccatin III (1) by way of a new and effective method for constructing oxetane ring. Thus, the synthesis of a precursor of taxol from novel taxoid 2 was accomplished.
- Shiina, Isamu,Saitoh, Masahiro,Nishimura, Koji,Saitoh, Katsuyuki,Mukaiyama, Teruaki
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p. 223 - 224
(2007/10/03)
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- Total synthesis of baccatin III and taxol
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An intramolecular Heck reaction (90 → 91) serves as the key step in the total synthesis of the titled compounds. The synthetic route is based on utilizing the Wieland-Miescher ketone (5) as a matrix to provide the C and D rings of the targets and to provide functionality implements for joining this sector to an A ring precursor (6). Catalytically induced enantiotopic control and early emplacement of the oxetane are other features of the route.
- Danishefsky, Samuel J.,Masters, John J.,Young, Wendy B.,Link,Snyder, Lawrence B.,Magee, Thomas V.,Jung, David K.,Isaacs, Richard C. A.,Bornmann, William G.,Alaimo, Cheryl A.,Coburn, Craig A.,Di Grandi, Martin J.
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p. 2843 - 2859
(2007/10/03)
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- Synthesis, conformational analysis, and biological evaluation of heteroaromatic taxanes
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The asymmetric syntheses of heteroaromatic 3-[(tert-butyldimethylsilyl)oxy]-2-azetidinones 12-16 via chiral ester enolate-imine cyclocondensation chemistry are described. The azetidinones contain heteroaromatic moieties which, in certain cases, contribute
- Georg, Gunda I.,Harriman, Geraldine C. B.,Hepperle, Michael,Clowers, Jamie S.,Vander Velde, David G.,Himes, Richard H.
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p. 2664 - 2676
(2007/10/03)
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- Total synthesis of Taxol. 1. Retrosynthesis, degradation, and reconstitution
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A successful strategy for the enantioselective synthesis of the natural stereoisomer of Taxol (1) has been developed. This strategy utilized the convergent assembly of Taxol's central eight-membered B ring from preformed synthons for rings A (10) and C (9) followed by late introduction of the D ring and side chain. Degradative studies confirmed the viability of certain crucial manipulations including oxidation of the C13 position (35 → 3) and regioselective introduction of the C1-hydroxyl, C2-benzoyloxy moiety (29 → 31). Additionally, a convenient method for the large-scale production of 29, a derivative useful for C2 analog production, was developed.
- Nicolaou,Nantermet,Ueno,Guy,Couladouros,Sorensen
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p. 624 - 633
(2007/10/02)
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- Facile AB ring cleavage reactions of taxoids
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Two facile B ring cleavage reactions of taxoids related to paclitaxel are reported. Treatment of a 13-chlorobaccatin with azide ion led to cleavage of the C-10/C-11 bond and formation of a hemiketal product. Treatment of a protected 2-debenzoyl paclitaxel with MnO2 yielded a ketoaldehyde in which the C-1/C-2 bond had been cleaved and the side chain had been eliminated.
- Chordia, Mahendra D.,Gharpure, Milind M.,Kingston, David G. I.
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p. 12963 - 12970
(2007/10/02)
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- Eine Totalsynthese von Taxol
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Keywords: Baccatin III; Heck-Reaktionen; Taxol; Totalsynthesen
- Masters, John J.,Link, J. T.,Snyder, Lawrence B.,Young, Wendy B.,Danishefsky, Samuel J.
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p. 1886 - 1888
(2007/10/03)
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- THE CHEMISTRY OF TAXANES: REACTIONS OF TAXOL AND BACCATIN DERIVATIVES WITH LEWIS ACIDS IN APROTIC AND PROTIC MEDIA
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Several Lewis acids were shown to cleanyl open the oxetane ring of taxol and baccatin derivatives.The reaction is shown to proceed via anchimeric assistance by the C-4 acetate group.Several minor products, including a novel derivative possessing a bridged C-ring, were also isolated.A mechanistric rationale is provides for all compounds formed.When taxol derivatives were treated with Lewis acids in methanol, ester cleavage reactions were observed.We provide conditions that are selective for C-10 acetate cleavage and for C-13 side-chain methanolysis.
- Chen, Shu-Hui,Huang, Stella,Wei, Jianmei,Farina, Vittorio
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p. 2805 - 2828
(2007/10/02)
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